$137 Find Cheap Flights from Greenville to Caribbean Islands - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Greenville to Caribbean Islands departing on 9/18. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Cheap Flights from Greenville to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$531
Santo Domingo
Santo Domingo1 stop$550
Montego Bay
Montego Bay1 stop$372
Oranjestad
Oranjestad1 stop$570
Nassau
Nassau1 stop$411
Kingston
Kingston1 stop$714
Simpson Bay
Simpson Bay1 stop$539
Providenciales
Providenciales1 stop$652
Port of Spain
Port of Spain1 stop$580
George Town
George Town1 stop$675
Willemstad
Willemstad1 stop$619
Aguadilla
Aguadilla1 stop$738
St. John's
St. John's1 stop$779
Punta Cana
Punta Cana1 stop$531
Santo Domingo
Santo Domingo1 stop$550
Montego Bay
Montego Bay1 stop$372
Oranjestad
Oranjestad1 stop$570
Nassau
Nassau1 stop$411
Kingston
Kingston1 stop$714
Simpson Bay
Simpson Bay1 stop$539
Providenciales
Providenciales1 stop$652
Port of Spain
Port of Spain1 stop$580
George Town
George Town1 stop$675
Willemstad
Willemstad1 stop$619
Aguadilla
Aguadilla1 stop$738
St. John's
St. John's1 stop$779

Book Cheap Greenville to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Greenville to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Greenville to Caribbean Islands

Sun, Oct 18 - Tue, Oct 20
Multiple Airlines Logo
1:29 pm - 11:38 pm
GSP
-
SJU
10h 09m
1 stop
Multiple Airlines Logo
4:39 pm - 7:44 pm
SJU
-
GSP
27h 05m
1 stop
$236Multiple Airlines
Mon, Aug 17 - Fri, Aug 21
Multiple Airlines Logo
4:57 pm - 4:11 pm
GSP
-
SJU
23h 14m
1 stop
Multiple Airlines Logo
6:35 am - 5:39 pm
SJU
-
GSP
11h 04m
1 stop
$270Multiple Airlines
Mon, Aug 24 - Thu, Aug 27
Multiple Airlines Logo
4:55 pm - 4:11 pm
GSP
-
SJU
23h 16m
1 stop
Multiple Airlines Logo
5:15 pm - 7:33 pm
SJU
-
GSP
26h 18m
1 stop
$273Multiple Airlines
Mon, Aug 24 - Thu, Aug 27
Multiple Airlines Logo
12:06 pm - 12:56 am
GSP
-
SJU
12h 50m
2 stops
Multiple Airlines Logo
5:15 pm - 7:33 pm
SJU
-
GSP
26h 18m
1 stop
$275Multiple Airlines
Fri, Dec 4 - Tue, Dec 8
Delta Logo
10:14 am - 4:35 pm
GSP
-
MBJ
6h 21m
1 stop
Delta Logo
6:00 pm - 11:37 pm
MBJ
-
GSP
5h 37m
1 stop
$372Delta
Fri, Oct 30 - Wed, Nov 4
Delta Logo
6:45 am - 12:07 pm
GSP
-
MBJ
6h 22m
1 stop
Delta Logo
3:45 pm - 11:37 pm
MBJ
-
GSP
7h 52m
1 stop
$392Delta
Fri, Oct 30 - Wed, Nov 4
American Airlines Logo
8:31 pm - 12:54 pm
GSP
-
MBJ
17h 23m
2 stops
American Airlines Logo
1:55 pm - 11:57 pm
MBJ
-
GSP
10h 02m
1 stop
$397American Airlines
Fri, Dec 4 - Tue, Dec 8
American Airlines Logo
5:25 am - 2:47 pm
GSP
-
MBJ
9h 22m
1 stop
American Airlines Logo
4:23 pm - 8:25 am
MBJ
-
GSP
16h 02m
2 stops
$442American Airlines
Thu, Sep 3 - Mon, Sep 7
United Airlines Logo
11:25 am - 12:50 am
GSP
-
POS
13h 25m
1 stop
United Airlines Logo
2:00 am - 3:03 pm
POS
-
GSP
13h 03m
1 stop
$580United Airlines
Sat, Oct 24 - Sat, Oct 31
United Airlines Logo
7:35 pm - 12:40 pm
GSP
-
AUA
17h 05m
1 stop
United Airlines Logo
2:00 pm - 10:46 pm
AUA
-
GSP
8h 46m
1 stop
$605United Airlines
Booking Insights

KAYAK's insights & trends for Greenville to Caribbean Islands flights

Get data-powered insights and trends into flights from Greenville to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Greenville to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $356, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Greenville to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Greenville to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Greenville to Caribbean Islands is September, when tickets cost $531 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $776 and $761 respectively.

How far in advance should I book a flight from Greenville to Caribbean Islands?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Greenville to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Greenville to Caribbean Islands, you should book around 6 weeks before departure, which saves you about 15% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Good to know

Low season

September

Cheapest flight

$137
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from Greenville to San Juan

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Greenville to Caribbean Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Greenville to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Greenville to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Greenville to Caribbean Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Greenville to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Greenville to Caribbean Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Greenville to Caribbean Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Greenville to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Greenville to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Greenville to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Greenville to Caribbean Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.8
DeltaOverall score based on 8478 reviews
7.8Comfort
8.1Boarding
7.8Entertainment
7.2Food
8.5Crew
Airline reviews

Flight delayed due to ground hold. Republic airways did a great job.

6.0 GoodSohail, Jul 2026
LGA - DCA
Read more Delta reviews

Flight delayed due to ground hold. Republic airways did a great job.

I missed the flight because the Minneapolis flight was 49 minutes LATE, and the Boise flight LEFT 24 minutes EARLY!

Our flight was delayed multiple times and then canceled at almost 1 in the morning. We are a family of 7, traveling with 5 young children. When the flight we were supposed to fly on finally arrived after waiting all day after an international flight into JFK we were informed our flight was in need of a copilot and once they located one we would take off. Then our flight was cancelled because the copilot was over his hours and they couldn't locate another. They knew before taking off from the previous location that the copilot would be unable to fly. They could have communicated the cancellation of the flight hours in advance. Once they cancelled and the pilot and copilot got off the flight, they joked about it. While there are understandably limits on flight time for pilots, they can still handle the situation in a professional manner. The late cancellation resulted in angry passengers that required police intervention in the airport. It also occurred so late and included other delta flights that after trying 15 different hotels, we were unable to secure a hotel room, they were all booked. No rental cars were available in the area either. We ended up staying in the airport with the 5 children. We made it home after 54 hours of travel with maybe 2 hours of sleep. Our luggage was lost and had to be claimed at the airport at our final destination. This was the worst trip I have ever taken and the worst airport I have ever spent time in. I met two individuals in the airport that were kind and helpful; Tonya Maingot Williams from the can we hel desk that worked to help get us rebooked and home, as well as provide us with care bags for our extended stay in the airport. The other individual was Danielle from Buffalo Wild Wings that was so very kind when we found a place to take our family we were traveling with to eat, all 11 of us and we were able to sit down together to enjoy a meal during such a stressful time.

This wasn't my experience with Delta. It was just the Pegasus flight. Seats were very hard. Staff was kinda rough. Not very nice. Charged me for snacks. For a 4 hour flight I would've expected more.

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

I just can’t understand why are you sell to many tickets ???? We had to wait 2 hours before 13 people from our flight take money and go to next day flight!

The only real hiccups in the flight were things beyond Delta’s control - turbulence which delayed food service and a departure delay caused by some VIP plane which stopped all departures and landings for 30 minutes - and was never explained to us by the crew. Otherwise good flight. I would fly Delta again.

The plane was frigid, and leaked water from the ceiling all over me and my seat.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

Flight was fine, but not having WiFi was a major negative

Everything was excellent and I enjoyed myself. Thank for everything

One of our group members was struggling to walk. In Charlotte we asked for a wheelchair and she was accompanied by Desmond. I was impressed by his patience and attention. In Boston she received the same service. I didn’t get the name of the helper but she went above and beyond in assisting us. A great AA service

I was trying to take 2 one and a half hour one way trips and I experienced almost 20 delays over the course of those two trips. Only a few of them were due to weather the rest was disorganization

Would have thought that they would gas up plane before everyone got on board

The flights were terribly delayed and then cancelled which forced us booking another night at the hotel. Very poor management from American Airlines

When my flight was delayed due to weather, I was rebooked to another flight since it showed that I would miss my connection. It was a lot of work to get back onto my originally connecting flight which was also delayed. That part caused a lot of stress and frustration. The ticketing agent at the desk was not very helpful.

American switched my flight to a 5 hour layover then cancelled my whole reservation with no notice and refused refund. Won’t fly with them again.

We sat on runway for an 1 hour because they were short handed at key west airport was not fun

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports